organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Ethyl 3-[1-(4-bromo­phen­yl)eth­yl­idene]carbazate

aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China, and bMicroscale Science Institute, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: liyufeng8111@163.com

(Received 26 October 2009; accepted 27 October 2009; online 31 October 2009)

In the crystal of the title compound, C10H11BrN2O2, the mol­ecules are linked by N—H⋯O hydrogen bonds, forming S(4) chains propagating in [100]. A C—H⋯O inter­action also occurs.

Related literature

For background to Schiff bases, see: Cimerman et al. (1997[Cimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145-153.]).

[Scheme 1]

Experimental

Crystal data
  • C10H11BrN2O2

  • Mr = 271.11

  • Orthorhombic, P c a 21

  • a = 7.6810 (15) Å

  • b = 5.9520 (12) Å

  • c = 24.750 (5) Å

  • V = 1131.5 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.62 mm−1

  • T = 293 K

  • 0.25 × 0.20 × 0.19 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: none

  • 10040 measured reflections

  • 2583 independent reflections

  • 1675 reflections with I > 2σ(I)

  • Rint = 0.116

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.152

  • S = 1.02

  • 2583 reflections

  • 140 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.45 e Å−3

  • Δρmin = −0.54 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1254 Friedel pairs

  • Flack parameter: −0.008 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1D⋯O1i 0.76 (10) 2.26 (10) 2.929 (6) 148 (10)
C3—H3A⋯O1i 0.96 2.43 3.242 (8) 142
Symmetry code: (i) [x-{\script{1\over 2}}, -y, z].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Related literature top

For background to Schiff bases, see: Cimerman et al. (1997).

Experimental top

A mixture of 1-(4-bromophenyl)ethanone (0.1 mol), and methyl carbazate (0.1 mol) was stirred in refluxing ethanol (20 mL) for 4 h to afford the title compound (0.085 mol, yield 85%). Colourless blocks of (I) were obtained by recrystallization from ethanol at room temperature.

Refinement top

The N-bound H atom was located in a difference map and freely refined. The other H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances=0.97 Å, and with Uiso=1.2–1.5Ueq.

Structure description top

For background to Schiff bases, see: Cimerman et al. (1997).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.
Ethyl 3-[1-(4-bromophenyl)ethylidene]carbazate top
Crystal data top
C10H11BrN2O2Dx = 1.591 Mg m3
Mr = 271.11Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 1982 reflections
a = 7.6810 (15) Åθ = 3.6–27.5°
b = 5.9520 (12) ŵ = 3.62 mm1
c = 24.750 (5) ÅT = 293 K
V = 1131.5 (4) Å3Block, colourless
Z = 40.25 × 0.20 × 0.19 mm
F(000) = 544
Data collection top
Bruker SMART CCD
diffractometer
1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.116
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
ω scansh = 98
10040 measured reflectionsk = 77
2583 independent reflectionsl = 3132
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.068P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.054
2583 reflectionsΔρmax = 0.45 e Å3
140 parametersΔρmin = 0.54 e Å3
1 restraintAbsolute structure: Flack (1983), 1254 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.008 (16)
Crystal data top
C10H11BrN2O2V = 1131.5 (4) Å3
Mr = 271.11Z = 4
Orthorhombic, Pca21Mo Kα radiation
a = 7.6810 (15) ŵ = 3.62 mm1
b = 5.9520 (12) ÅT = 293 K
c = 24.750 (5) Å0.25 × 0.20 × 0.19 mm
Data collection top
Bruker SMART CCD
diffractometer
1675 reflections with I > 2σ(I)
10040 measured reflectionsRint = 0.116
2583 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152Δρmax = 0.45 e Å3
S = 1.02Δρmin = 0.54 e Å3
2583 reflectionsAbsolute structure: Flack (1983), 1254 Friedel pairs
140 parametersAbsolute structure parameter: 0.008 (16)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.44214 (8)0.19577 (12)0.58046 (2)0.0815 (3)
C80.3535 (7)0.2162 (9)0.5091 (2)0.0584 (13)
C10.0415 (10)0.3211 (12)0.1630 (3)0.080 (2)
H1A0.04950.31710.13640.120*
H1B0.03440.45900.18300.120*
H1C0.15260.31210.14540.120*
N10.1035 (6)0.0551 (8)0.27043 (18)0.0548 (10)
C70.3861 (7)0.0435 (10)0.4736 (2)0.0600 (12)
H7A0.45170.07980.48450.072*
C20.1408 (6)0.1185 (9)0.23832 (19)0.0515 (11)
O20.0223 (6)0.1363 (9)0.19887 (18)0.0724 (12)
C90.2600 (7)0.4010 (9)0.4932 (2)0.0610 (12)
H9A0.23850.51770.51720.073*
C40.1498 (6)0.2404 (8)0.3496 (2)0.0463 (10)
C50.2249 (6)0.2378 (8)0.4043 (2)0.0470 (10)
N20.1849 (5)0.0686 (7)0.31978 (17)0.0509 (9)
C100.1984 (6)0.4113 (9)0.4408 (2)0.0542 (11)
H10A0.13740.53810.42970.065*
C60.3215 (7)0.0544 (9)0.4220 (2)0.0552 (12)
H6A0.34280.06370.39830.066*
O10.2632 (5)0.2456 (6)0.24299 (17)0.0611 (9)
C30.0382 (7)0.4343 (10)0.3314 (3)0.0633 (14)
H3A0.00010.40900.29500.095*
H3B0.10470.57070.33290.095*
H3C0.06130.44690.35470.095*
H1D0.017 (13)0.111 (17)0.276 (4)0.10 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1019 (5)0.0934 (5)0.0491 (3)0.0009 (3)0.0070 (4)0.0089 (4)
C80.057 (3)0.067 (3)0.051 (3)0.003 (2)0.007 (2)0.008 (2)
C10.099 (5)0.077 (5)0.063 (4)0.003 (3)0.014 (3)0.023 (3)
N10.049 (2)0.066 (3)0.050 (2)0.004 (2)0.0056 (19)0.007 (2)
C70.063 (3)0.060 (3)0.057 (3)0.010 (2)0.006 (2)0.008 (2)
C20.050 (3)0.059 (3)0.045 (2)0.006 (2)0.003 (2)0.003 (2)
O20.070 (2)0.085 (3)0.062 (3)0.011 (2)0.024 (2)0.020 (2)
C90.073 (3)0.055 (3)0.056 (3)0.004 (3)0.008 (2)0.015 (3)
C40.040 (2)0.051 (2)0.049 (3)0.0062 (19)0.0064 (19)0.001 (2)
C50.039 (2)0.047 (2)0.055 (3)0.0015 (18)0.0064 (19)0.004 (2)
N20.048 (2)0.057 (2)0.047 (2)0.0031 (17)0.0013 (16)0.002 (2)
C100.055 (3)0.045 (3)0.063 (3)0.0062 (19)0.003 (2)0.007 (2)
C60.058 (3)0.057 (3)0.051 (3)0.009 (2)0.003 (2)0.009 (2)
O10.055 (2)0.064 (2)0.065 (2)0.0031 (18)0.0094 (16)0.0121 (18)
C30.061 (3)0.058 (3)0.070 (4)0.008 (2)0.007 (2)0.002 (3)
Geometric parameters (Å, º) top
Br1—C81.896 (6)C2—O21.339 (6)
C8—C91.372 (8)C9—C101.380 (7)
C8—C71.376 (7)C9—H9A0.9300
C1—O21.421 (8)C4—N21.289 (6)
C1—H1A0.9600C4—C51.473 (7)
C1—H1B0.9600C4—C31.507 (7)
C1—H1C0.9600C5—C101.387 (7)
N1—C21.335 (7)C5—C61.391 (7)
N1—N21.374 (6)C10—H10A0.9300
N1—H1D0.75 (10)C6—H6A0.9300
C7—C61.371 (7)C3—H3A0.9600
C7—H7A0.9300C3—H3B0.9600
C2—O11.212 (6)C3—H3C0.9600
C9—C8—C7120.7 (5)C10—C9—H9A120.5
C9—C8—Br1120.5 (4)N2—C4—C5115.8 (4)
C7—C8—Br1118.8 (4)N2—C4—C3123.8 (5)
O2—C1—H1A109.5C5—C4—C3120.4 (4)
O2—C1—H1B109.5C10—C5—C6117.2 (5)
H1A—C1—H1B109.5C10—C5—C4122.3 (4)
O2—C1—H1C109.5C6—C5—C4120.5 (4)
H1A—C1—H1C109.5C4—N2—N1117.4 (4)
H1B—C1—H1C109.5C9—C10—C5121.9 (5)
C2—N1—N2118.5 (4)C9—C10—H10A119.1
C2—N1—H1D129 (7)C5—C10—H10A119.1
N2—N1—H1D103 (7)C7—C6—C5121.6 (5)
C8—C7—C6119.6 (5)C7—C6—H6A119.2
C8—C7—H7A120.2C5—C6—H6A119.2
C6—C7—H7A120.2C4—C3—H3A109.5
O1—C2—N1126.4 (5)C4—C3—H3B109.5
O1—C2—O2123.2 (5)H3A—C3—H3B109.5
N1—C2—O2110.4 (5)C4—C3—H3C109.5
C2—O2—C1116.5 (5)H3A—C3—H3C109.5
C8—C9—C10119.0 (5)H3B—C3—H3C109.5
C8—C9—H9A120.5
C9—C8—C7—C61.3 (8)C3—C4—C5—C6177.1 (5)
Br1—C8—C7—C6179.3 (4)C5—C4—N2—N1173.9 (4)
N2—N1—C2—O115.0 (8)C3—C4—N2—N15.5 (7)
N2—N1—C2—O2164.9 (5)C2—N1—N2—C4178.4 (5)
O1—C2—O2—C12.8 (9)C8—C9—C10—C51.5 (8)
N1—C2—O2—C1177.1 (6)C6—C5—C10—C92.0 (8)
C7—C8—C9—C100.2 (8)C4—C5—C10—C9175.8 (4)
Br1—C8—C9—C10179.5 (4)C8—C7—C6—C50.8 (8)
N2—C4—C5—C10180.0 (4)C10—C5—C6—C70.8 (7)
C3—C4—C5—C100.6 (7)C4—C5—C6—C7177.0 (5)
N2—C4—C5—C62.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O1i0.76 (10)2.26 (10)2.929 (6)148 (10)
C3—H3A···O1i0.962.433.242 (8)142
Symmetry code: (i) x1/2, y, z.

Experimental details

Crystal data
Chemical formulaC10H11BrN2O2
Mr271.11
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)7.6810 (15), 5.9520 (12), 24.750 (5)
V3)1131.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)3.62
Crystal size (mm)0.25 × 0.20 × 0.19
Data collection
DiffractometerBruker SMART CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10040, 2583, 1675
Rint0.116
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.152, 1.02
No. of reflections2583
No. of parameters140
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.45, 0.54
Absolute structureFlack (1983), 1254 Friedel pairs
Absolute structure parameter0.008 (16)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O1i0.76 (10)2.26 (10)2.929 (6)148 (10)
C3—H3A···O1i0.962.433.242 (8)142
Symmetry code: (i) x1/2, y, z.
 

Acknowledgements

The authors would like to thank the Science Foundation of Weifang University (No. 2009Z24).

References

First citationBruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCimerman, Z., Galic, N. & Bosner, B. (1997). Anal. Chim. Acta, 343, 145–153.  CrossRef CAS Web of Science Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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